1,2-Dimethoxyethane → HCID 57597488, 화합물

HRID 1786707노트

반응식

HRID 1786707 반응식
C([C:3]1[C:4](Br)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])C.[C:13]([C:16]1[CH:17]=[C:18](OB(O)O)[CH:19]=[CH:20][CH:21]=1)(=[O:15])[CH3:14].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH2:37]([CH2:40]OC)OC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[CH2:37]([O:8][C:6]([C:5]1[C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:13](=[O:15])[CH3:14])[CH:17]=2)=[CH:10][CH:11]=[CH:3][CH:4]=1)=[O:7])[CH3:40]

참가 물질

8

반응물 5

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 23030395HCID 23030395, 화합물HCID 230304032-Bromo-3-ethylbenzoic acid

생성물 1

HCID 57597488HCID 57597488, 화합물수율 95%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of ethyl 2-bromobenzoic acid (10.0 g) and 3-acetylphenylboric acid (7.87 g) in dimethoxyethane (200 ml) was added 2 N sodium carbonate solution (50 ml), and the mixture was deaerated and argon-substituted. To this mixture was added tetrakis(triphenylphosphine) palladium (0) (5.04 g), and the mixture was heated to reflux for 15 hours. The obtained reaction mixture was subjected to cooling, and distributed between ethyl acetate (400 ml) and saturated sodium bicarbonate solution (400 ml). The aqueous layer was further extracted with ethyl acetate (200 ml), and the combined organic layer was washed with saturated brine, dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to give the title compound as a yellow oil (11.08 g, 95%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 hours
  3. customThe obtained reaction mixture
  4. temperatureto cooling
  5. extractionThe aqueous layer was further extracted with ethyl acetate (200 ml)
  6. washthe combined organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-dbbb1c6c81804f80891a6abbf08e6b2f
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507753B2

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